Unapologetically non-normal

I ran the San Francisco Marathon this July in 3:05, averaging about 60 miles a week with a coach. Kahlil ran 2:49 on about 30 miles a week. When I told him that was a hot take, he doubled down: you don't need the miles, you need faster workouts and a handful of long runs, and everybody who says otherwise is doing it out of habit. And by the way, he does Ironmans as well. Casual.

I still think he's wrong about the mileage. But I’ve come to think that exchange tells you a lot about him as a CEO. Most founders in a hot category build the me-too version and hope to out-execute. Kahlil decided on day one that Natural would own the entire payments stack, from ledger to charter, which is not how a reasonable person starts a payments company. It's how someone who believes they can run 2:49 on thirty miles a week (and then actually does) starts a payments company.

You need some level of crazy for either.

It's all about the people

In investing, it's all about the people. An oversimplification for sure, but in my belief, there are three reasons why someone wants to be a founder: to get rich, to be famous, or to make an impact. There are much easier ways to achieve the first two, but to pound your head against the wall, day after day, for a decade, you have to have some level of ambition that goes beyond money and fame. At Maveron, we have a phrase for it: unapologetically non-normal. The most exceptional founders are built a little different. They see the future before anyone else can, and they beat their own drum getting there.

In fact, we score for this. We have an entrepreneur scorecard where we rate founders on a scale of 1 to 4 across energy positivity, a spiky skill set, all-star recruiting, a gift for communication, and total obsession. In five and a half years, very few founders have scored high across the board.

I first met Kahlil in 2022 when he pitched us Ivella, a fintech for couples. We didn't invest. But the note I wrote to myself afterward wasn't about the deal. It was: stay close to this guy, because he is going to do something great. Whether or not it was Ivella, there was a large venture in him.

What I’ve missed

I've loved a lot of the investing job. Five and a half years at Maveron gave me a front-row seat to thousands of companies and the people building them. But there were three things from my operating years that I kept missing, and they got louder the longer I stayed.

The first is ownership: the feeling that whether the company succeeds or fails is partly on you. The second is working intimately with a team, day in and day out. The third is the intellectual debate about where the world is going, paired with the chance to be on the ground floor actually enacting it. I got a taste of all three at YouTube, where I helped launch our subscriptions business, YouTube Red. It took me longer than it should have to admit I wanted that back.

When I started picking my head up and thinking about what I'd want to join, I remembered those conversations with Kahlil and sent him a note to catch up.

The catch-up

The catch-up was on a Wednesday. We talked about what drives me, what I want out of life, and marathon times, which is how I learned I'd gotten fast enough to even be in the same conversation. I told him I was still figuring out whether I want to go back to operating. He said I should meet his co-founders. I suggested two weeks later, when I'd be in SF. He asked if I was free Friday. Two days later I was on a call with Walt and Eric, and came away as impressed with them as I was with him.

That urgency wasn't new. When we'd caught up after Ivella, he told me he'd walked away from an earnout because of how much conviction he had in what came next. That thing became Natural.

Two weeks later I was in SF with the rest of the team. Three things stuck with me:

Talent density. Kahlil mentioned in passing that of the twenty people they've hired, nobody has ever turned down an offer. After years of listening to founders talk about recruiting, that struck me.
The people it attracts. One night around 9pm, still at my desk, I overheard a debate about fraud: once a business has many users and each user has many agents, identity stops being one-to-one, so where does trust actually live? When you're creating a new category, nobody has the answers yet. Nobody pretended to, and nobody was leaving until they got closer to one. That's the kind of person who chooses to work at Natural.
Speed. I walked in expecting a company less than a year old to have a prototype and a deck. Instead they'd built the guts of a payments company from scratch, the ledger, the compliance stack, and everything in between, and it was already running.

Hard to unsee

I flew back to New York and went back to my day job. As a consumer investor I evaluate B2C and B2B2C companies, and that week, I kept catching myself asking a question in pitch meetings: when do these companies start moving money programmatically, and are they a future Natural customer? Once you see every company that way, it's hard to unsee it.

The data scientist in me had a separate reaction. I've always had a bias for businesses that accumulate a data moat. Natural's ledger is one: every payment carries the verified entity behind it, what the agent was trying to do, and what it actually did. That gets more valuable with volume and time.

The last piece was more personal. When these companies do decide to move money, why would they choose Natural? The thesis I've built my investing around is that brand is the moat, and it's only gotten truer: as technology becomes a commodity, what's left is trust, taste, and distribution. I've been telling founders that from the other side of the table for years. I wanted to be on the side that has to make it true. So I'm joining as the founding GTM hire, working with startups and developers building with agents.

The bet

The next generation of applications will be built on primitives that are being decided right now, and the cost of watching that happen from the outside was higher than the cost of being wrong. I'm self-aware enough to know there's a lot of risk ahead. Owning the whole stack from day one is non-normal, the same way running a 2:49 on 30 miles a week is.

I never used to be a runner. I ran one marathon on a whim, got hooked, and have three marathons this year to go sub-three. That's how I do things. Once I'm in, I'm all in. Natural is what I'm all in on now.

If this sounds like your kind of challenge, we're hiring: /careers.